Oakland Vacations from $458
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was $588, price is now $458 per person
$458
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
Right near the bus terminal so it can get sketchy walking around. Loved the washer and dryer in the room. Heads up to bring unscented detergent if fragrances bother you.
Reviewed on Jul 2, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Save 100% on your flight
Price was $1,042, price is now $730 per person
$730
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
It was just ok. Maybe Pittsburgh needs to get a Ritz or Four Seasons.
Reviewed on Jun 24, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $663, price is now $510 per person
$510
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,543 reviews)
Great location and room. Staff was great!
Reviewed on Jul 6, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was $658, price is now $512 per person
$512
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,074 reviews)
good location, average and old facility
Reviewed on Jul 1, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,278 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Jul 9 to Jul 10
$145 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (785 reviews)
"Parking is expensive. But if you're a weekend traveler you can park on the street for free."
Reviewed on Jul 6, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $242 total per night from Jul 12 to Jul 13
$242 total
Jul 12 - Jul 13
Total with taxes and fees
9.2/10 Wonderful! (791 reviews)
"I found the property to be excellent in all phases, from cleanliness to staff. A wonderful experience and I will definately stay again when in Pittsburgh."
Reviewed on Jul 1, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
$110 nightly
The price is $125 total per night from Aug 2 to Aug 3
$125 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Parking was easy and hotel was decently clean could’ve been improved. But staff was super helpful and restaurant/ bar in lobby was amazing."
Reviewed on Jul 6, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Oakland attractions
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$47
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
per adult
Explore a world of travel with Expedia
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- Visit Downtown Pittsburgh
- Schenley Park
- Carnegie Museum of Art
- Strip District Vacations
- Cathedral of Learning
- Pittsburgh Vacations
- Carnegie Mellon University
- North Shore Vacations
- National Aviary
- Acrisure Stadium
- Carnegie Library of Pittsburgh
- Byham Theater
- Carnegie Science Center
- Grandview Overlook
- Andy Warhol Bridge
- Children's Museum of Pittsburgh
- Monongahela Incline
- Senator John Heinz Regional History Centre
- Lighthouse ArtSpace Pittsburgh
- Visit Pittsburgh
- Duquesne Incline
- University of Pittsburgh
- Phipps Conservatory
- Ppg Paints Arena
- Kennywood
- Where to stay in Pittsburgh
- Roberto Clemente Bridge
- Andy Warhol Museum
- Petersen Events Center
- Point State Park
- The Nationality Rooms
- David L Lawrence Convention Center
- U.s. Steel Tower
- Heinz Memorial Chapel
- Soldiers and Sailors Memorial Hall and Museum
- Market Square
- Pnc Park
- Photo Antiquities Museum of Photographic History
- Carnegie Museum of Natural History
- Rachel Carson Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.